I don't think Gon is blowing (messing up) anything if his intention is to ask her out. They're both mature adults with some experience presumably, regardless of whether it was successful experience or not. Projecting a little here but if she says no, Gon gon' be a little sad, but more glad that he worked up the courage to ask her out anyway.
The more you try, the less severe the rejection will hit. And you can say even that it's not a rejection, if she wants to remain friends with Gon. In a short period of time, he can get over it, reconnect as friends, and lose that romantic inclination, but gain a good friend, as they've proven to be quite compatible. There are people that are just better off as friends rather than romantic partners, and that's not a bad thing.